These are the homework exercises to accompany the Textmap for McMurry's Organic Chemistry textbook.
Predict the product of a nucleophilic substitution of (S)-2-bromopentane reacting with CH3CO2-, Show stereochemistry.
What product(s) do you expect from the reaction of 1-bromopentane with each of the following reagents in an SN2 reaction?
A – KI
B – NaOH
C - CH3C≡C-Li
D – NH3
Which in the following pairs is a better nuceophile?
A - (CH3CH2)2N- or (CH3CH2)2NH
B - (CH3CH2)3N or (CH3CH2)3B
C – H2O or H2S
Order the following in increasing reactivity for an SN2 reaction.
CH3CH2Br CH3CH2OTos (CH3CH2)3CCl (CH3CH2)2CHCl
Solvents benzene, ether, chloroform are non-polar and not strongly polar solvents. What effects do these solvents have on an SN2 reaction?
A - (CH3CH2)2N- as there is a charge present on the nitrogen.
B - (CH3CH2)3N because a lone pair of electrons is present.
C - H2O as oxygen is more electronegative.
They will decrease the reactivity of the reaction.
Give the products of the following SN1 reaction. Show stereochemistry.
Rank the following by increasing reactivity in an SN1 reaction.
3-bromo-1-pentene and 1-bromo-2-pentene undergo SN1 reaction at almost the same rate, but one is a secondary halide while the other is a primary halide. Explain why this is.
Label the following reactions as most likely occuring by an SN1 or SN2 mechanism. Suggest why.
Consider the stability of the intermediate, the carbocation.
A < D < B < C (most reactive)
They have the same intermediates when you look at the resonance forms.
A – SN1 *poor leaving group, protic solvent, secondary cation intermediate
B – SN2 *good leaving group, polar solvent, primary position.
Ignoring the alkene stereochemistry show the elimination product(s) of the following compounds:
What is the product of the following molecule in an E2 reaction? What is the stereochemistry?
The stereochemistry is (Z) for the reaction.
Which of the following compounds will react faster in an E2 reaction; trans-1-bromo-2-isopropylcyclohexane or cis-1-bromo-2-isopropylcyclohexane?
The cis isomer will react faster than the trans. The cis isomer has two possible perpendicular hydrogen in which it can eliminate from.
Label the following reactions as SN1, SN2, E1, or E2.
A – SN2
B – E1
C – SN1
D – E2